Pentanoic Acid → Pentanamide

Participants

Reaction Conditions

Reaction Steps

Valeric acid (10.86 mL, 100 mmol, 1.0 eq) was dissolved in chloroform (100 mL, 0.1 M) and cooled to -20° C. Ethyl chloroformate (9.52 mL, 100 mmol, 1 eq) was added. Triethylamine (14.0 mL, 100 mmol, 1.0 eq) was then added dropwise over 5 minutes. The mixture was stirred at -20° C. for 30 minutes. Ammonia was bubbled through the mixture 10 minutes at -20° C. and 20 minutes at 0° C. The mixture was then allowed to warm to room temperature and stirred for 90 minutes. Chloroform (100 mL) and 1 N hydrochloric acid (50 mL) were added. The layers were separated and the organic layer was washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and freed of solvent in vacuo. Trituration with isopropyl ether gave the title compound (6.315 g, 62%) as a white solid.

Provenance & Evidence